Indoleamine-2, 3-dioxygenase (IDO) is an enzyme that catalyzes the addition of oxygen to the essential amino acid tryptophan to form N-formylkynurenine. It has been found in high levels among cancer patients and linked to a decline in T cells. Inhibiting the function of this enzyme with small molecule inhibitors could improve the effectiveness of chemotherapy by promoting a more robust immune response to developing tumors. Hydroxylamines have been found to be successful inhibitors of IDO. Based on the results of tested compounds and computer modeling, compounds with diphenyl rings and electron withdrawing groups have been found to be particularly effective. A variety of these hydroxylamine compounds were synthesized using several different methods, including the Mitsunobu reaction and transition metal catalyzed hydroalkoxylation.

Synthesis of hydroxylamines as indoleamine-2, 3-dioxygenase inhibitors

244th National Meeting (2012)

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